Biological evaluation of 23-dichloro-5,8-dimethoxy-1,4-naphthoquinone as an anti-breast cancer agent

Anticancer Research

Volumn 29, Issue 1, 2009, Pages 191-199

  Kanaan, Yasmine M ^b   Das, Jharna R ^a   Bakare, Ladapo ^a   Enwerem, Nkechi M ^a   Berhe, Solomon ^a   Beyene, Desta ^b   Williams, Vonita ^b   Zhou, Yanfei ^c   Copeland Jr , Robert L ^a,d  

^a Department of Pharmacology ^*

^b Department of Microbiology

^c HOWARD UNIVERSITY   (United States)

^d HOWARD UNIVERSITY COLLEGE OF MEDICINE   (United States)

Author keywords

23 Dichloro 5,8 Dimethoxy 1,4 naphthoquinone; Apoptosis; Cell cycle; Cytotoxicity; Estrogen positive negative breast cancer cell lines

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2,3 DICHLORO 5,8 DIMETHOXY 1,4 NAPHTHOQUINONE; DNA TOPOISOMERASE; RETINOBLASTOMA PROTEIN; UNCLASSIFIED DRUG; 2,3-DICHLORO-5,8-DIMETHOXY-1,4-NAPHTHOQUINONE; ANTINEOPLASTIC AGENT; NAPHTHOQUINONE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER CELL CULTURE; CELL CYCLE ARREST; CELL CYCLE REGULATION; CELL CYCLE S PHASE; CELL STRAIN MCF 7; CELL VIABILITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; CULTURE MEDIUM; DRUG EFFECT; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; BREAST TUMOR; CELL CYCLE; CELL SURVIVAL; DRUG ANTAGONISM; ENZYMOLOGY; FLOW CYTOMETRY; METABOLISM; TUMOR CELL LINE; WESTERN BLOTTING;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BLOTTING, WESTERN; BREAST NEOPLASMS; CELL CYCLE; CELL LINE, TUMOR; CELL SURVIVAL; DNA TOPOISOMERASES, TYPE I; FLOW CYTOMETRY; HUMANS; NAPHTHOQUINONES;

EID: 61449266755     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (29)

1. Perera NM and Gui GP: Multi-ethnic differences in breast cancer: current concepts and future directions. Int J Cancer 106: 463-467, 2003.
2. Jemal A, Siegel R, Ward E, Hao Y, Xu J, Murray T and Thun MJ: Cancer statistics, 2008. CA Cancer J Clin 58: 71-96, 2008.
3. Parkin DM, Bray F, Ferlay J and Pisani P: Estimating the world cancer burden: Globocan 2000. Int J Cancer 94: 153-156, 2001.
4. American Cancer Society: Cancer Facts and Figures 2001. Atlanta: American Cancer Society, 2001.
5. Chen VW, Correa P, Kurman RJ, Wu XC, Eley JW, Austin D, Muss H, Hunter CP, Redmond C, Sobhan M, Coates R, Reynolds P, Herman AA and Edwards EK: Histological characteristics of breast carcinoma in blacks and whites. Cancer Epidemiol Biomarkers Prev 3: 127-135, 1994.
6. Early Breast Cancer Trialists Collaborative Groups: Effect of chemotherapy and hormonal therapy for early breast cancer on recurrence and 15-year survival: an overview of randomized trials. Lancet 356: 1687-1717, 2005.
7. Jordan VC and Gradishar WJ: Molecular mechanisms and future uses of antiestrogens. Mol Aspects Med 18: 167-247, 1997.
8. Labrie F, Labrie C, Belanger A, Simard J, Gauthier S, Luu-The V, Merand Y, Giguere V, Candas B, Luo S, Martel C, Singh SM, Founder M, Coquet A, Richard V, Charbonneau R, Charpenet G, Tremblay A, Tremblay G, Cusan L and Veilleux R: EM-652 (SCH 57068), a third-generation SERM acting as pure antiestrogen in the mammary gland and endometrium. J Steroid Biochem Mol Biol 69: 51-84, 1999.
9. Miller MG, Rodgers A and Cohen GM: Mechanisms of toxicity of naphthoquinones to isolated hepatocytes. Biochem Pharmacol 35: 1177-1184, 1986.
10. Foglesong PD, Reckord C and Swink S: Doxorubicin inhibits human DNA topoisomerase I. Cancer Chemother Pharmacol 30: 123-125, 1992.
11. D'Arpa P and Liu LF: Topoisomerase-targeting antitumor drugs. Biochim Biophys Acta 989: 163-177, 1989.
12. Fujii N, Yamashita Y, Arima Y, Nagashima M and Nakano H: Induction of topoisomerase II-mediated DNA cleavage by the plant naphthoquinones plumbagin and shikonin. Antimicrob Agents Chemother 36: 2589-2594, 1992.
13. Yang F, Chen Y, Duan W, Zhang C, Zhu H and Ding J: SH-7, a new synthesized shikonin derivative, exerting its potent antitumor activities as a topoisomerase inhibitor. Int J Cancer 119: 1184-1193, 2006.
14. Krishnan P and Bastow KF: Novel mechanisms of DNA topoisomerase II inhibition by pyranonaphthoquinone derivatives eleutherin, alpha lapachone, and beta lapachone. Biochem Pharmacol 60: 1367-1379, 2000.
15. Wang JC: DNA topoisomerases. Annu Rev Biochem 54: 665-697, 1985.
16. Habib NS, Bekhit AA and Park JY: Synthesis and biological evaluation of some new substituted naphthoquinones. Boll Chim Farm 142: 232-238, 2003.
17. Chung Y, Shin YK, Zhan CG, Lee S and Cho H: Synthesis and evaluation of antitumor activity of 2- and 6-[(1,3-benzothiazol-2-yl)aminomethyl]-5,8- dimethoxy-1,4-naphthoquinone derivatives. Arch Pharm Res 27: 893-900, 2004.
18. Bakare O, Ashendel CL, Peng H, Zalkow LH and Burgess EM: Synthesis and MEK1 inhibitory activities of imido-substituted 2-chloro-1,4-naphthoquinones. Bioorg Med Chem 11: 3165-3170, 2003.
19. Copeland, Jr. RL, Das JR, Bakare O, Enwerem NM, Berhe S, Hillaire K, Douglas White D, Beyene D, Kassim K and Kanaan YM: Cytotoxicity of 2,3-dichloro-5,8-dimethoxy-1,4-naphtho-quinone in androgen-dependent and -independent prostate cancer cell lines. Anticancer Res 27: 1537-1546, 2007.
20. Sun SY, Hail N Jr and Lotan R: Apoptosis as a novel target for cancer chemoprevention. J Natl Cancer Inst 96: 662-672, 2004.
21. Pommier Y, Sordet O, Antony S, Hayward RL and Kohn KW: Apoptosis defects and chemotherapy resistance: molecular interaction maps and networks. Oncogene 23: 2934-2949, 2004.
22. Nakagawa H, Tsuta K, Kiuchi K, Senzaki H, Tanaka K, Hioki K and Tsubura A: Growth inhibitory effects of diallyl disulfide on human breast cancer cell lines. Carcinogenesis 22: 891-897, 2001.
23. Yang YP, Kuo HS, Tsai HD, Peng YC and Lin YL: The p53-dependent apoptotic pathway of breast cancer cells (BC-M1) induced by the bis-type bioreductive compound aziridinyl-naphthoquinone. Breast Cancer Res 7: R19-27, 2005.
24. Hou Y, Guo T, Wu C, He X and Zhao M: Effect of shikonin on human breast cancer cells proliferation and apoptosis in vitro. Yakugaku Zasshi 126: 1383-1386, 2006.
25. Cummings J and Smyth JF: DNA topoisomerase I and II as targets for rational design of new anticancer drugs. Ann Oncol 4: 533-543, 1993.
26. Walker PR, Smith C, Youdale T, Leblanc J, Whitfield JF and Sikorska M: Topoisomerase II-reactive chemotherapeutic drugs induce apoptosis in thymocytes. Cancer Res 51: 1078-1085, 1991.
27. Chen J, Huang YW, Liu G, Afrasiabi Z, Sinn E, Padhye S and Ma Y: The Cytotoxicity and mechanisms of 1,2-naphthoquinone thiosemicarbazone and its metal derivatives against MCF-7 human breast cancer cells. Toxicol Appl Pharmacol 197: 40-48. 2004.
28. Wang X, Nakagawa-Goto K, Bastow KF, Don MJ, Lin YL, Wu TS and Lee KH: Antitumor agents. 254. Synthesis and biological evaluation of novel neo-tanshinlactone analogues as potent antibreast cancer agents. J Med Chem 49: 5631-5634, 2006.
29. Kamesaki S, Kamesaki H, Jorgensen TJ, Tanizawa A, Pommier Y and Cossman J: Bcl-2 protein inhibits etoposide-induced apoptosis through its effects on events subsequent to topoisomerase II-induced DNA strand breaks and their repair. Cancer Res 53: 4251-4256, 1993.